N-[5-tert-Butyl-4-methyl-3H-thiazol-(2Z)-ylidene]-5-chloro-2-nitro-benzenesulfonamide | 612536-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-[5-tert-Butyl-4-methyl-3H-thiazol-(2Z)-ylidene]-5-chloro-2-nitro-benzenesulfonamide
• CAS: 612536-81-9
• 化学式: C₁₄H₁₆ClN₃O₄S₂
• 分子量: 389.884
• InChiKey: VOZRODPOKORWSH-UHFFFAOYSA-N

物化性质

• 沸点：
  541.4±60.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105.43
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[5-tert-Butyl-4-methyl-3H-thiazol-(2Z)-ylidene]-5-chloro-2-nitro-benzenesulfonamide 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 13.5h， 生成 2-amino-N-(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)-5-chlorobenzenesulfonamide
  参考文献：
  名称：

  Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure–activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives

  摘要：

  In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K 103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 101 and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 muM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.045
• 作为产物：
  描述：

  5-Tert-butyl-4-methyl-1,3-thiazol-2-amine;hydrochloride 、 5-氯-2-硝基苯磺酰氯 在 吡啶 作用下， 反应 12.0h， 以41%的产率得到N-[5-tert-Butyl-4-methyl-3H-thiazol-(2Z)-ylidene]-5-chloro-2-nitro-benzenesulfonamide
  参考文献：
  名称：

  Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure–activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives

  摘要：

  In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K 103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 101 and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 muM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.045